Top 10 Awkward Date Moments on Seinfeld

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Top 10 Awkward Date Moments on Seinfeld

VOICE OVER: Rebecca Brayton WRITTEN BY: Cassondra Feltus
"Seinfeld" had plenty of awkward moments, especially when it game to dating! For this list, we'll be looking at the times when characters' love lives got a little too cringe. Our countdown includes when George dates a female Jerry, when Jerry proposes a “Ménage à Trois," Sidra's spectacular chest, and more!
Transcript
"Seinfeld" had plenty of awkward moments, especially when it game to dating! For this list, we’ll be looking at the times when characters’ love lives got a little too cringe. Our countdown includes when George dates a female Jerry, when Jerry proposes a “Ménage à Trois," Sidra's spectacular chest, and more! What moment made you uncomfortable the most? Let us know in the comments.

#10: George Lies About Being a Marine Biologist

“The Marine Biologist”

When Jerry runs into George’s college crush Diane, he says that George is now a marine biologist. Impressed, she gets his number. And even though he’s frustrated with Jerry for giving him a pretend career, George goes along with it. He and Diane spend their first (and only) date at the beach where he recites “facts” about sea creatures. Just his luck, they come across a crowd of onlookers worried about a beached whale. Diane puts him on the spot in front of everyone, fully expecting him to intervene. All George can do is awkwardly head into the water. Miraculously, he does save the whale by dislodging a golf ball from its blowhole. But when he tells Diane the truth, she’s no longer impressed.

#9: Aaron, the Close Talker

“The Raincoats”

What’s more awkward than someone (especially a stranger) invading your personal space? Elaine’s boyfriend Aaron knows no boundaries, and is what Jerry calls a “close talker.” And it doesn’t take long for the Seinfelds to understand what he means. Aaron is the nicest guy, but maybe a little too nice. He clearly loves people, so much so that he needs to be as close as possible when talking to them. Elaine can’t help but wonder why he’s going out of his way to show Jerry’s parents a good time while they’re in New York. He gets so worked up when they finally leave that it’s more than a little off putting. Maybe a little distance isn't such a bad thing.

#8: Sidra’s Spectacular Chest

“The Implant”

Jerry’s smitten with Sidra Holland, a beautiful woman at the health club. Elaine suggests she has breast implants. But when Sidra’s obviously natural breasts break her fall in the sauna, Elaine discovers she was mistaken. Pleased with this “good” news, Jerry asks Sidra out again. At his apartment, Jerry awkwardly broaches the topic of big bosoms, commenting on the sizes of “women today” and the deceased Jayne Mansfield. Despite his awkward conversation, he almost gets to “experience” Sidra’s chest for himself. But Kramer and Elaine stop by unannounced. Realizing that Elaine must’ve fallen on purpose in an attempt to test the authenticity of her breasts, Sidra immediately leaves. But not before delivering one of the show’s most iconic lines.

#7: It’s Not You, It’s Me

“The Lip Reader”

When Jerry and George go to a tennis match, George is unknowingly captured on TV stuffing his face full of sundae. His girlfriend Gwen breaks up with him, possibly because she saw the unflattering on-screen appearance. She gives him the old “it’s not you, it’s me” line. After the breakup, George has to see her at their mutual friend Todd’s party. Here’s where Jerry’s new love interest comes in. Laura is deaf and is able to read lips pretty well. And George hatches a plan to have her read Gwen’s lips at the party to see what she says about him. In true “Seinfeld” fashion, there’s a misunderstanding that leads George to make a fool of himself.

#6: The Blue Condom

“The Fix-Up”

Jerry and Elaine set up the desperate and hopeless George with the bitter Cynthia since they’re both discouraged by the dating scene. They’re reluctant to be fixed up but give it a shot anyway. Their talk on the phone goes well, though George is upset that Cynthia didn’t tell Elaine about the quality of the conversation. They end up having sex on their first date and it wasn’t great. The kitchen is a weird place to start getting intimate with someone. And Cynthia thinks so, too, because she leaves shortly after. There’s a pregnancy scare, and Elaine suspects George might’ve used one of Kramer’s colorful (and likely defective) condoms. George’s supportiveness woos Cynthia, but once she sees the way he eats, she’s clearly disgusted.

#5: Jerry Proposes a “Ménage à Trois”

“The Switch”

Having a sense of humor is usually at the top of everyone’s “must-haves” for a partner. And for Jerry, a comedian, it’s non-negotiable. It bugs him that Sandy doesn’t laugh, and is essentially humorless, making for dull, awkward exchanges. Her roommate, on the other hand, does laugh at Jerry’s jokes. He now wants to pull a “roommate switch.” Jerry explains his predicament to George, and after pulling an all-nighter, comes up with a plan — a threesome. Jerry’s suggestion to Sandy goes much better than he expected. But ultimately, it’s just not him.

#4: George & the Answering Machine

“The Phone Message”

After George has a great date with his new love interest Donna, she invites him up for coffee. Not considering that she may just want him to come in for something more intimate than caffeine, George declines the offer. He immediately regrets his response, kicking himself for potentially missing out on sex. Jerry and Elaine encourage him to call her, but he gets her machine. Watching George leave the first message was cringe itself, but we can only imagine what the subsequent aggressive messages sounded like. George convinces Jerry to help him swap out the machine tapes. Donna definitely doesn’t make it easy for them and they fumble through the plan. But it turns out she already heard the messages and thought they were hilarious!

#3: George Dates a Female Jerry

“The Cartoon”

George finds himself in some “weird trouble” when Elaine and Kramer tell him that his new girlfriend Janet looks exactly like Jerry. He somehow missed it before, but now that’s all he sees when he looks at her. George stresses over their relationship being mainly physical, and Janet reminds him that he complimented her looks when they first met. He desperately tries to find some common ground in their relationship, but it seems to be based on physical attraction. And when Janet gets gum stuck in her hair and cuts it really short, her resemblance to Jerry becomes undeniable and George literally runs away from her.

#2: Love & a Big Matzo Ball

“The Face Painter”

When you tell someone you love them, you kind of expect a certain response. George takes a big step with his girlfriend Siena, and professes his love for her. But sadly, she’s more interested in eating. George is both relieved and irritated when he learns that she has bad hearing in her left ear. Siena must’ve not heard him. So, after kissing in his car, he says it again. And this time, he makes sure it’s in her right ear. But guess what — she did hear him say it the first time and she still doesn’t say it back. Ouch.

Before we unveil our top pick, here are a few honorable mentions.

Jerry’s Disgusted With Shelly, “The Doodle”

An Overreaction Would Be an Understatement

Taking Credit for the Big Salad, “The Big Salad”

The Pettiness Is Strong With George

Lanette & the Dude, “The Summer of George”

Picking up Your Date Who Just Showered With Someone Else…Not Awkward at All, Right?

Gillian’s Man Hands, “The Bizarro Jerry”

Jerry Just Can’t Get Past the Hands

Marisa Tomei Punches George, “The Cadillac”

George Tells the Movie Star He’s Actually Engaged

#1: Phil Totola Takes “It” Out

“The Stand-In”

Poor Elaine. She really can’t catch a break in the dating department. The guys she meets seem relatively normal at first. But there’s always a creep factor lurking below the surface. Jerry sets her up with his friend Phil, someone he really thinks she’ll hit it off with. Clearly, the two had a great time because they couldn’t stop laughing. All is well until Phil unexpectedly exposes himself to Elaine. We’re just as horrified as she is at that moment. Luckily for us, we didn’t have to actually see “it.”
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